Benzaldehyde → HCID 86758067, compound

HRID 1934751Notes

Reaction equation

HRID 1934751 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][CH:4]=[C:5]1[CH2:20][CH2:19][C:8]2([S:12][CH2:11][C:10](=[O:13])[N:9]2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:7][CH2:6]1.[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CC(C)([O-])C.[K+].Cl>O1CCCC1.C(OCC)(=O)C.O>[CH3:1][CH:2]([CH3:21])[CH2:3][CH:4]=[C:5]1[CH2:20][CH2:19][C:8]2([S:12][C:11](=[CH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:10](=[O:13])[N:9]2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:7][CH2:6]1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 224671633-[8-(3-Methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]-propionic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 86758067HCID 86758067, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 5 ml of anhydrous tetrahydrofuran was dissolved 0.50 g of 3-[8-(3-methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]-propionic acid. After adding 0.25 ml of benzaldehyde and 0.45 g of potassium tert-butoxide at ambient temperature, the resulting mixture was heated under reflux for 6 hours. The reaction mixture was poured into a mixture of water and ethyl acetate, pH was adjusted to 2.0 with 2 mol/L hydrochloric acid, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Isopropyl ether was added to the residue and the deposited crystal was collected by filtration. Thus, 0.32 g of 3-[8-(3-methylbutylidene)-3-oxo-2-(1-phenylmethylidene)-1-thia-4-azaspiro[4.5]decan-4-yl]-propionic acid was obtained as a colorless crystalline product.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 6 hours
  3. customthe organic layer was separated
  4. washThe organic layer was washed successively with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionIsopropyl ether was added to the residue
  8. filtrationthe deposited crystal was collected by filtration

Sources & evidence

ORD record
ord-f2cfb4fa9cc64a21a4f98e4e09e8110f
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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